MCQEasyJEE 2023Aromatic Compounds & Benzene

JEE Chemistry 2023 Question with Solution

The correct sequence of reagents for the preparation of Q and R is:

Reaction scheme asking reagent sequence for conversion of compound P to products Q and R, with labels P, Q, and R shown in the figure.
  • A

    (i) CrO3\mathrm{CrO_3}, 770K770 \, \text{K}, 20atm20 \, \text{atm}; (ii) CrO2Cl2\mathrm{CrO_2Cl_2}, H+\mathrm{H^+}; (iii) NaOH\mathrm{NaOH}; (iv) H3O+\mathrm{H_3O^+}

  • B

    (i) CrO2Cl2\mathrm{CrO_2Cl_2}, H3O+\mathrm{H_3O^+}; (ii) CrO3\mathrm{CrO_3}, 770K770 \, \text{K}, 20atm20 \, \text{atm}; (iii) NaOH\mathrm{NaOH}; (iv) H3O+\mathrm{H_3O^+}

  • C

    (i) KMnO4\mathrm{KMnO_4}, OH\mathrm{OH^{--}}; (ii) MoO3\mathrm{MoO_3}, Δ\Delta; (iii) NaOH\mathrm{NaOH}; (iv) H3O+\mathrm{H_3O^+}

  • D

    (i) MoO3\mathrm{MoO_3}, Δ\Delta; (ii) CrO2Cl2\mathrm{CrO_2Cl_2}, H3O+\mathrm{H_3O^+}; (iii) NaOH\mathrm{NaOH}; (iv) H3O+\mathrm{H_3O^+}

Answer

Correct answer:A

Step-by-step solution

Standard Method

Given: A reaction sequence asks for the correct reagents for the preparation of Q and R from P.

Find: The correct option giving the reagent sequence.

From the solution, the sequence is stated as follows:

  1. Step 1: Oxidation of benzene to benzoquinone using CrO3\mathrm{CrO_3} at 770K770 \, \text{K} and 20atm20 \, \text{atm}.
  2. Step 2: Formation of phenol by further oxidation with CrO2Cl2\mathrm{CrO_2Cl_2} in acidic medium.
  3. Step 3: Neutralization with NaOH\mathrm{NaOH} to form phenoxide ion.
  4. Step 4: Acidification with H3O+\mathrm{H_3O^+} to yield phenol.

Thus, the reagent order is:

\mathrm{CrO_3},\ 770\,K,\ 20\,atm \; \rightarrow \; CrO_2Cl_2/H^+ \; \rightarrow \; NaOH \; \rightarrow \; H_3O^+}

This matches Option A.

Therefore, the correct option is A.

Common mistakes

  • Choosing the option with the correct reagents but in the wrong order. This is incorrect because multistep organic conversions depend on sequence. Match each reagent to the stated step before selecting the option.

  • Confusing acidic workup with the oxidation step. H3O+\mathrm{H_3O^+} is used for acidification after base treatment, not as the primary oxidizing reagent. Keep reaction conditions separated by function.

  • Ignoring the final NaOH\mathrm{NaOH} and H3O+\mathrm{H_3O^+} sequence. This is wrong because base treatment followed by acidification is a distinct transformation step. Do not stop after identifying only the first oxidizing reagent.

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